Ducoffs.comAirlines Flying this Route
Ducoffs.com compares full-service and low-cost airlines flying between Chicago and Naples in a single search, including nonstop and one-stop options, so you can weigh price against total travel time.
ORD → NAP
Find and Compare the Cheapest Ways to Fly from Chicago to Naples
Compare one-way, round-trip and flight + hotel packages from Chicago to Naples, a nonstop flight of about 10h 25m, with fares from around 550.
Chicago to Naples flight facts
Chicago to Naples is an international route covering about 4,930 miles, arriving at Naples International Airport (NAP) in Italy. Peak travel season in Naples runs June–August (mild, long sunny days), while November–March is usually the quietest and best-value time to visit.
| Departing from | O'Hare International Airport (ORD) |
|---|---|
| Arriving at | Naples International Airport (NAP) |
| Distance | 4,930 miles (7,939 km) |
| Nonstop flight time | About 10h 25m |
| Round-trip fares from | $550 (estimate) |
| Cheapest months | September, February, January |
| Peak season in Naples | June–August |
| Cheapest hotel months in Naples | November–March |
| Best time to book | 2 to 6 months ahead |
| Route info updated | October 16, 2026 |
When to visit Naples
Peak season
June–August
Mild, long sunny days
Shoulder season
April–May & September–October
Cool and crisp, fewer crowds
Off-peak season
November–March
Cold, damp and grey
Estimated round-trip fares by month, Chicago to Naples
| Month | Fares from |
|---|---|
| January | $610 |
| February | $555 |
| March | $630 |
| April | $680 |
| May | $625 |
| June | $735 |
| July | $770 |
| August | $765 |
| September | $550 |
| October | $665 |
| November | $650 |
| December | $840 |
Flying from Chicago to Naples
Best Time to Book Flights from Chicago to Naples
Fares on this route tend to be lowest in September, February, and January. For the best selection, book about 2 to 6 months before departure and stay flexible by a day or two.
Average Travel Duration
Chicago and Naples are about 4,930 miles apart. A nonstop flight takes roughly 10h 25m; connecting itineraries usually add 2 to 5 hours.
Chicago to Naples flight questions
How can I find the absolute cheapest flight from Chicago to Naples?
The best way to secure budget rates is by comparing multiple airlines simultaneously and checking flexible dates. Ducoffs.com scans available partner networks to bring you real-time pricing options.
What is the cheapest month to fly from Chicago to Naples?
Based on typical seasonal demand, September, February, and January tend to offer the lowest fares on this route, with estimated round-trip prices starting around $550. Live prices change daily, so run a search for your exact dates.
How long is the flight from Chicago to Naples?
Chicago and Naples are about 4,930 miles apart. A nonstop flight takes roughly 10h 25m, while connecting itineraries usually add 2 to 5 hours depending on the layover.
When are hotels cheapest in Naples?
Hotel rates in Naples are usually lowest in November–March, when demand is quieter, and highest during peak season (June–August). Booking your flight and hotel together can save up to 30%.
Which airport do I fly into for Naples?
This route arrives at Naples International Airport (NAP). Your search results also show nearby airports when they offer a cheaper or faster option.
How far in advance should I book a flight to Naples?
For this route, booking about 2 to 6 months before departure usually gives the best balance of price and seat selection. Mid-week departures are often cheaper than weekend flights.
Is it cheaper to bundle flights and hotels together?
Yes. Bundling your travel components can save you up to 30% compared to booking flights and hotels separately, as airlines and properties offer exclusive package discounts.
Travel guides for this trip
- PlanningThe Cheapest Months to Fly from Miami, New York, Los Angeles, Chicago, Tampa, Dallas, and AtlantaWhen airfare is lowest from Miami, New York, Los Angeles, Chicago, Tampa, Dallas, and Atlanta, plus the routes that see the biggest seasonal price swings.
- DealsHow to Find Hidden Hotel Deals with Ducoffs TravelTwelve proven ways to pay less for great hotels: smarter dates, bundles, neighborhood swaps, call-in rates, and how to use Ducoffs.com tools to find them.
- PlanningHow to Stretch Your Vacation Days into Longer TripsTurn a few vacation days into long trips by pairing them with public holidays and weekends, and avoid the peak prices that come with holiday travel.